Photo Tour: Havana

Join award-winning street photographer Steve Simon and Cuban photographer and guide Juan Carlos Ocana for an unforgettable week of living and breathing photography in beautiful Havana, Cuba.

Tour Outline

This 6-day masterclass (limited to 10 students) will take you to some of the most picturesque, interesting and exciting locations on and off the beaten path within Havana and beyond.

Steve will teach you new and powerful street photography techniques guaranteed to push you out of your comfort zone and up to new heights in your work.

He will share his personal photography philosophies gleaned from a lifetime of wandering urban landscapes with his camera.


We will also discuss the laws and ethics of street photography while defining a strategy for capturing the rich daily life on the street, overcoming fears and shyness, approaching strangers, framing, juxtaposition, and layering.


Cost per Person: USD 5,500 (approximately AED 20,205 depending on your bank’s conversion rate) for single-occupancy. Please contact us if you are planning to travel with a companion and would like a shared room rate.


Round-trip airfare from Miami, Florida to Havana, accommodation, breakfast, lunch, dinner, transportation, transfers, daily instruction and critiques, Cuban Visa license and paperwork (not fees) required for American citizens travelling to Cuba. Other nationalities do not have these restrictions and may apply directly, further details provided in the Travel Information section.


International flights to/from Miami, visas/visa fees, alcoholic beverages, incidentals, and personal expenditures.

Arrival Day: Flight from Miami to Havana followed by Arrival & Orientation.

We will be met at the Havana airport by Juan Carlos, and a bus will take us to the Parque Central Hotel in Old Havana. We will then have an introductory meet and greet followed by a quick-start session with tips on shooting and editing. This will be followed by a photo walk with Cuban photographers Juan Carlos Ocana and Vladimir Rivera along Prado Avenue as we discuss what we will see and do this week along with shooting tips and the realities of being a street photographer in Havana. We will end at the water along The Malecón when the late daylight offers prime light for shooting before returning to the hotel for dinner.


Day 2: Overview and Nighttime Shoots in Old Havana

We start the day with an early morning shoot led by a local Cuban photographer, followed by a lecture and critique at the hotel where we will introduce participants by seeing a brief portfolio of their work, followed by a view of the work of some of the best and most influential street photographers from Cuba and the world. You are encouraged to edit and choose your top six images from that morning (and the previous day’s shoot) for critique. 

After the group critique, we will drive through Havana touring some of the most interesting and scenic locations and getting a taste of what’s to come. We will shoot as we go and stop to photograph at several pre-selected locations. We will have a local Cuban photographer accompany us each day to share their experiences and insight into photographing the streets of Havana.


In the evening we will have a nighttime street shoot amidst the music, dance, and nightlife of Old Havana. We will also shoot architecture and visit Arms Square.


Day 3: The Rafael Trejo Boxing Club in Old Havana

We will start the day with an early morning shoot in Old Havana with a local Cuban photographer, following which we will meet for a lecture and critique at the hotel.

We will then head to shoot at the Rafael Trejo Boxing Club in Old Havana, an open-air training facility where some of Cuba’s world-class boxers trained. There we will have great access and great light as we meet and photograph local boxers, trainers and coaches.


Later in the day we will resume shooting street photography in Old Havana where we will meet and speak with locals during our street portrait assignments. 


Day 4: Driving Tour and Street Photography

In a trio of convertible classic cars, we will drive through Havana, touring some of the most interesting and scenic locations in Old Havana and shooting as we go. We will stop at several pre-selected locations to shoot along the way.

In the afternoon, we will have a lecture, critique and meeting with a local Cuban photographer back at our hotel.


After the group critique, we will hit the streets during the golden light in a new section of Old Havana. A local Cuban photographer will accompany and guide us.



Day 5: Cuban National Ballet School and Havana Harbor

We will open the day with early morning street photography in Old Havana before meeting for a lecture and critique at the hotel. Afterwards, we will go to the Cuban National Ballet School, the largest in the world and the most prestigious in Cuba. This school is a training facility, not a performance venue, so we will have great access to meet and photograph the dancers while taking their portraits.


Later that day we will have another opportunity to shoot street photography in Odl HAvana before going to visit a local gallery to learn about Cuba’s vibrant photography scene.


After supper, we will enjoy the vibrant nightlife of old Havana as we embark on a photowalk of Havana Harbor with a local Cuban photographer


Day 6: One-Hour Shoots and Final Critique

We will start the day with a bus ride to several pre-selected locations for one-hour shoots.

Possible locations include: The Callejon de Hamel, where vivid and colorful murals, outdoor sculptures and shrines dedicated to the Afro-Cuban religion of Santeria cover the entire small block, the other end of the Malecón, The American Embassy Area, San Francisco Square, The Cigar Factory.


On this final day of the tour, we will meet for a final lecture, critique, recap, and group slideshow presentation to highlight work created during the week. You will provide your final edit of up to 30 images from the week, and Steve will edit it down to the final 15 per person for the final slide show. Steve will later send you a copy of the slideshow that will be posted on and Vimeo.


We will close our last day with an optional Cathedral Square photowalk.


Day 7: Return to Miami

We will meet for breakfast before heading back to the airport for our return flights to Miami.


*Timings and schedules may be adjusted according to weather or other unforeseen events.*

Travel Information:

If you have any questions leading up to the trip, please feel email them across to with the title “Inform me re: Havana Tour Meetup.”



Our staff will arrive in Miami at least 1 day before travelling to Cuba. We will take a chartered flight from Miami to Havana, on the morning of departure day - January 16.  We strongly recommend allowing  a full day in Miami both before and after the scheduled tour dates to allow for any unforeseen events. Please keep us informed of your arrival and departure plans so we can coordinate with you. 



Our staff will leave Havana on a chartered flight on the morning of January 22.  We strongly recommend allowing a full day in Miami both before and after the scheduled tour dates to allow for any unforeseen events. Please keep us informed of your arrival and departure plans so we can coordinate with you. 



New Regulations: All UAE, Saudi, Oman, Bahraini residents must apply for a Cuban visa through the Cuban Embassy in Saudi. 


  • “Tourist Card”  up to date information, please see here.
  • A Tourist Card is valid only for one entry within 180 days after the date of issue.
  • It is valid for a 30-day stay in Cuba, extendable in Cuba for a further 30 days maximum.
  • Documents: Applicants are required to send documents and the completed application form to the Saudi Embassy.
  • Cost: SAR 360, and the Cuban Embassy in Saudi recommends using DHL to courier the documents and fee.
  • Turnaround Time: 30-40 days.
  • Please note that in addition to the usual plane ticket/hotel booking, the embassy requires a 3-month bank statement and an employer sponsor letter.
  • Accommodation in places other than hotels or tourist resorts requires authorization from Cuban Local Immigration Authorities to be requested in Cuba.


1. All Photo Tour participants will be required to sign a compulsory GPP waiver of liability prior to departure, as per standard practice.

2. This workshop requires a minimum of 6 attendees by December 15th to run. If the minimum is not reached, you will be refunded 90% of the workshop fee.

What to Bring
  •  The weather in Cuba is often beautiful, and while it can be a bit humid, the average high temperature in January is 26°C with an average low of 16°C. The weather does cool down in the evenings - please bear this in mind when packing. Do also consider bringing sunscreen.
  • A portfolio of 12 images – JPEGS on a USB flash drive in a folder entitled “[Your Name]”  for critique. Images file names should contain your name as well.
  • This is a digital workshop, so a DSLR, Mirrorless, High-End Compact or rangefinder camera will all work. Having a backup body is always a good idea.
  • For your DSLR or Mirrorless, fast prime lenses are ideal, or at least one wide-angle zoom. Lenses in the classic range for street photography: 28mm, 35mm, 50mm, 85mm will all work (based on full frame camera) and fast lenses f2 or faster offer more flexibility.
  • Two or three fully-charged batteries & charger.
  • More memory cards than you think you will need and a  card reader.
  • Your own laptop for image editing and note-taking.
  • A flash is optional but bring one to experiment with flash on the street.
Cancellation Policy

More than 60 days prior to the start of the Tour: Full refund less 10% admin charge

Between 60 and 30 days prior to the start of the Tour: 50% refund

Later than 30 days prior to the start of the Tour: No refund possible

Stay up to date

Follow this class to get an email the next time it's scheduled

Notify Me

Who Should Attend

You love vibrant sights and bustling streets! You are confident using your camera in Aperture Priority or Manual mode. If you would like to join this tour but do not yet have the skills described, consider taking our Photography - Level 1 workshop to bring you up to speed.